Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether → HCID 67730996, compound

HRID 2396230Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[Si:19]([O:26][C@H:27]1[CH2:36][C@H:35](O)[C@H:34]2[C:29]([CH:30]=[CH:31][C@H:32]([CH3:55])[C@@H:33]2[CH2:38][CH2:39][C@H:40]2[O:45][C:44](=[O:46])[CH2:43][C@H:42]([O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[CH2:41]2)=[CH:28]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>>[Si:19]([O:26][C@H:27]1[CH2:36][C@H:35]([O:11][C:10](=[O:12])[C:9]([O:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:16][CH:15]=2)([CH3:13])[CH3:14])[C@H:34]2[C:29]([CH:30]=[CH:31][C@H:32]([CH3:55])[C@@H:33]2[CH2:38][CH2:39][C@H:40]2[O:45][C:44](=[O:46])[CH2:43][C@H:42]([O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:49])[CH3:50])[CH2:41]2)=[CH:28]1)([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:21])[CH3:20]

Participants

Reactant 2

HCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether

HCID 18988544HCID 18988544, compound

Product 1

HCID 67730996HCID 67730996, compoundYield 80.6%

Procedure

A procedure similar to that described in Example 1, above, was followed, but using 786 mg of 2-(4-trifluoromethylbenzyloxy)-2-methylpropionic acid and 1.10 g of (4R,6R)-6-{(1S,2S,6S,8S,8aR)-2-[1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above], to give 1.28 g of the title compound as a colorless foam.

Sources & evidence

ORD record: ord-50978186aaf544738a58d483ff245c0f
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491167

Reaction notes

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